Singer and fiddler Caitlin Cary got her start playing with the well-known but tumultuous alt-country band Whiskeytown, and set out on a solo career after Whiskeytown disbanded in 2000. Her solo work has attracted the attention of such musical luminaries as singer-songwriter Mary Chapin Carpenter, as well as listeners and critics alike.

Cary was born on October 28, 1968, in Seville, Ohio, the youngest child in a family with six older brothers. Her father was an amateur instrument maker, and she grew up in a musical home; she began studying violin when she was six, and also played her songs on her father's homemade harpsichords. She told Charlie Melvin in England's Birmingham Post, "His harpsichords never lasted more than a couple of years, but then he'd go build another one."

In addition to music, Cary was also interested in writing, and enrolled in North Carolina State University's graduate program in creative writing. While working on her master's degree and teaching part-time, Cary's life was changed when a friend suggested she play with the alt-country band Whiskeytown. The friend knew Ryan Adams, founder of the band, and suggested to Adams that he contact Cary. According to Melvin, Adams called her and said, "I'm starting this band and we're practicing tomorrow, can you come over?"

Cary had never considered a career in music, and told Wes Orshoski in Billboard, "I had absolutely no rock 'n' roll fantasy whatsoever. When I got the call, I was like, 'Oh, cool, we'll have some fun on the weekends.'"

Whiskeytown would prove to be a volatile and often-changing band, but during its tumultuous history the band released three albums that received critical acclaim, Faithless Street,Rural Free Delivery, and Stranger's Almanac. Cary and Adams were the only members of Whiskeytown who remained with the band from beginning to end. "We managed to stick it out when no one else could," she told Melvin. And she added, "I still believe that one day we'll make a great record together, of country duets or something." Cary married Whiskeytown drummer Eric "Skillet" Gilmore.

When Whiskeytown disbanded in 2000, Cary knew she was interested in a solo career, but was unsure whether she could make it on her own. At first, she thought she might get a record deal from Whiskeytown's label, Outpost, but the company folded and the deal fell through. Nevertheless, Cary began writing and recording her own songs, ultimately releasing them as When You Weren't Looking, her full-length solo debut album on Yep Roc, an independent record label based in Chapel Hill, North Carolina. Cary told Melvin, "Yep Roc came to the table with a very nice deal and convinced me they were working really hard and that I would be taken seriously." However, she still harbored doubts about the project, and told Orshoski that despite her success in getting the contract, "I got this feeling that somebody was gonna walk through the door and bust me and totally realize that I'm a fraud."

Cary was assisted in the project by former Whiskeytown member Mike Daly, who co-wrote and played on most of the album's tracks. Cary told Orshoski that the fact that she knew Daly so well helped her enormously in her work with him. Because she doesn't play guitar or piano, she had to sing the songs over and over while he worked out the chords that would fit them best. The album also included two songs written by Whiskeytown's former frontman, Ryan Adams. This connection with Whiskeytown, Yep Roc manager Glenn Dicker told Orshoski, "gives a little more legitimacy to Whiskeytown and Caitlin herself." Orshoski also speculated that this would increase the album's sales. In Interview, Ray Rogers characterized the album as a "knockout," and praised Cary's strong delivery and clear voice. Melvin noted that the album attracted the attention of well-known singer-songwriter Mary Chapin Carpenter, who posted a message on Cary's website, saying that she liked the album so much she had purchased 20 copies to give to friends. In addition, when Cary played in Chapin's hometown of Charlottesville, Virginia, Chapin Carpenter came to the show, and Cary asked her if she would join in with Cary on "Pony," Chapin Carpenter's favorite song on the album. Chapin Carpenter enthusiastically agreed.

Although Cary took two years to create While You Weren't Looking, she wrote her second Yep Roc album, I'm Staying Out, in three months. It was released 13 months after her debut album, when Yep Roc insisted it was time for her to make another record. Cary was startled, assuming that she would be able to take more of a break between albums, but as she told Walter Tunis in an article for the Knight Ridder/Tribune News Service, "They were like, 'Hey, people are liking you. It's time to do this again.'" Tunis wrote that despite the speed with which Cary wrote it, I'm Staying Out did not seem rushed. He called it "a contemplative, rich album brimming with luxurious songs." Tunis particularly praised the album's title song, "which should distance Cary from her more brooding contemporaries."

Cary told Tunis that she had noticed that some other singers, particularly women, sounded self-absorbed or precious, something that she worked hard to avoid. "This whole 'Woe is me, my boyfriend just hurt my feelings' thing is OK for a couple of songs. But I don't like to listen to whole records of them." Cary also noted that she was indebted to her experience with Whiskeytown, which opened up many opportunities for her, and also helped her become more savvy about the music business. "As rocky as the road was, I felt very fortunate to have been down it," she said.

by Kelly Winters

Caitlin Cary's Career

Played with Whiskeytown, 1994-2000; began solo career, 2000; released debut album, When You Weren't Looking, 2002; released album, I'm Staying Out, 2003.